Iodine-catalyzed chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines: A short synthesis of Kumujian-C, Eudistomin-U, Norharmane, Harmane Harmalan and Isoeudistomine-M

被引:26
作者
Gaikwad, Sunil [1 ]
Kamble, Dayanand [1 ]
Lokhande, Pradeep [1 ]
机构
[1] Savitribai Phule Pune Univ, Ctr Adv Studies, Dept Chem, Pune 411007, Maharashtra, India
关键词
Dehydrogenation; Aromatization; Iodine; Carbolines; Kumujian-C; Eudistomin-U; BIOLOGICAL EVALUATION; CARBAZOLE ALKALOIDS; EFFICIENT SYNTHESIS; ROOM-TEMPERATURE; FORMAL SYNTHESIS; DERIVATIVES; UTILITY; DESIGN; HETEROCYCLES; CYCLIZATION;
D O I
10.1016/j.tetlet.2018.04.043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Temperature controlled chemoselective dehydrogenation and aromatization of tetrahydro-beta-carbolines, using molecular I-2 and H2O2, in DMSO solvent affords a practical access to a series of corresponding 3,4-dihydro-beta-carbolines and beta-carbolines respectively. This method has been successfully employed in the short synthesis of Kumujian-C, Eudistomin-U, Norharmane Harmane Harmalan and Isoeudistomin-M. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2387 / 2392
页数:6
相关论文
共 65 条
[21]   An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins [J].
Kamal, Ahmed ;
Sathish, Manda ;
Prasanthi, A. V. G. ;
Chetna, Jadala ;
Tangella, Yellaiah ;
Srinivasulu, Vunnam ;
Shankaraiah, Nagula ;
Alarifi, Abdullah .
RSC ADVANCES, 2015, 5 (109) :90121-90126
[22]   PhI(OAc)2-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I [J].
Kamal, Ahmed ;
Tangella, Yellaiah ;
Manasa, Kesari Lakshmi ;
Sathish, Manda ;
Srinivasulu, Vunnam ;
Chetna, Jadala ;
Alarifi, Abdullah .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) :8652-8662
[23]   Design and Synthesis of C3-Pyrazole/Chalcone-Linked Beta-Carboline Hybrids: Antitopoisomerase I, DNA-Interactive, and Apoptosis-Inducing Anticancer Agents [J].
Kamal, Ahmed ;
Srinivasulu, Vunnam ;
Nayak, V. Lakshma ;
Sathish, Manda ;
Shankaraiah, Nagula ;
Bagul, Chandrakant ;
Reddy, N. V. Subba ;
Rangaraj, Nandini ;
Nagesh, Narayana .
CHEMMEDCHEM, 2014, 9 (09) :2084-2098
[24]   3 NEW BETA-CARBOLINES FROM THE BERMUDIAN TUNICATE EUDISTOMA-OLIVACEUM [J].
KINZER, KF ;
CARDELLINA, JH .
TETRAHEDRON LETTERS, 1987, 28 (09) :925-926
[25]   EUDISTOMINS A, D, G, H, I, J, M, N, O, P, AND Q, BROMO-BETA-CARBOLINES HYDROXY-BETA-CARBOLINES PYRROLYL-BETA-CARBOLINES AND 1-PYRROLINYL-BETA-CARBOLINES FROM THE ANTIVIRAL CARIBBEAN TUNICATE EUDISTOMA-OLIVACEUM [J].
KOBAYASHI, J ;
HARBOUR, GC ;
GILMORE, J ;
RINEHART, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (05) :1526-1528
[26]   Rapid and selective deallylation of allyl ethers and esters using iodine in polyethylene glycol-400 [J].
Konda, Shankaraiah G. ;
Humne, Vivek T. ;
Lokhande, Pradeep D. .
GREEN CHEMISTRY, 2011, 13 (09) :2354-2358
[27]   EUDISTOMINS FROM THE NEW-ZEALAND ASCIDIAN RITTERELLA-SIGILLINOIDES [J].
LAKE, RJ ;
BLUNT, JW ;
MUNRO, MHG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (07) :1201-1206
[28]   A Facile Synthesis of 3-Substituted 9H-Pyrido[3,4-b]indol-1(2H)-one Derivatives from 3-Substituted β-Carbolines [J].
Lin, Guowu ;
Wang, Yue ;
Zhou, Qingfa ;
Tang, Weifang ;
Wang, Jian ;
Lu, Tao .
MOLECULES, 2010, 15 (08) :5680-5691
[29]   Dimethylsulfoxide-iodine catalysed deprotection of 2′-allyloxychalcones:: synthesis of flavones [J].
Lokhande, PD ;
Sakate, SS ;
Taksande, KN ;
Navghare, B .
TETRAHEDRON LETTERS, 2005, 46 (09) :1573-1574
[30]   Aromatization and Halogenation of 3,3a,4,5-Tetrahydro-3-aryl-2-phenyl-2H-benzo[g]indazole Using I2/DMSO, CuCl2/DMSO, and N-Bromosuccinimide [J].
Lokhande, Pradeep D. ;
Hasanzadeh, Kamal ;
Khaledi, Hamid ;
Ali, Hapipah Mohd .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (06) :1398-1406